Oakland Vacations from $416
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Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Pittsburgh Downtown
Downtown Pittsburgh
Price was $513, price is now $416 per person
$416
per person
Apr 3 - Apr 5
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.2/10 Very Good! (3,142 reviews)
Staff were outstanding, and very helpful. Pool and hot tub was nice to have, especially the hot tub. Food in the hotel restaurant was OK, but nothing spectacular.
Reviewed on Feb 6, 2026
Red Roof Inn PLUS+ Pittsburgh East - Monroeville
Save 100% on your flight
Price was $670, price is now $477 per person
$477
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pittsburgh (PIT)
6/10 (1,007 reviews)
Convenient price?Well and nice staff and clean
Reviewed on Feb 4, 2026
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Price was $815, price is now $631 per person
$631
per person
Apr 3 - Apr 5
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
Staff and amenities were great! We loved our room. However, it looks like there were some drinks left in the mini fridge from the patron before us. Other than this, we had a wonderful stay.
Reviewed on Jan 10, 2026
Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
Price was $648, price is now $527 per person
$527
per person
Apr 3 - Apr 5
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Very friendly staff and clean room.
Reviewed on Feb 1, 2026
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $130 total per night from Feb 23 to Feb 24
$130 total
Feb 23 - Feb 24
Total with taxes and fees
9/10 Wonderful! (598 reviews)
Room was clean and beautiful. Nice walk in shower. Staff was very friendly and helpful.
Reviewed on Feb 5, 2026
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $227 total per night from Feb 18 to Feb 19
$227 total
Feb 18 - Feb 19
Total with taxes and fees
9.2/10 Wonderful! (740 reviews)
Very clean, convenient, upscale, and great restaurant. Enjoyed free drink coupons on arrival!
Reviewed on Jan 20, 2026
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
Fully refundable
$118 nightly
The price is $135 total per night from Feb 12 to Feb 13
$135 total
Feb 12 - Feb 13
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
very clean and wonderful service.
Reviewed on Jan 19, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Oakland
University of Pittsburgh
4.5/5(843 reviews)
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Carnegie Museum of Natural History
4.5/5(48 reviews)
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Carnegie Museum of Art
5/5(4 reviews)
If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.
Things to do
Pittsburgh Pirates Baseball Game at PNC Park
$67
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
Pittsburgh: Beauty of the Burgh Bike Tour
$59
per adult
94% of travellers recommend
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- University of Pittsburgh
- University of Pittsburgh Medical Center
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- Petersen Events Center
- Cathedral of Learning
- Soldiers and Sailors Memorial Hall and Museum
- Carnegie Museum of Natural History
- Heinz Memorial Chapel
- Carnegie Museum of Art
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- Schenley Park
- Carnegie Mellon University
- Hunt Institute for Botanical Documentation
- Pittsburgh Opera
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- Clemente Museum
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- Contemporary Craft
- Market Square
- Visit Pittsburgh
- South Side Vacations
- PPG Paints Arena
- Temple Sinai
- Senator John Heinz Regional History Centre
- Duquesne University
- Walnut Street
- Western Pennsylvania Sports Museum
- Visit Shadyside
- Roberto Clemente Bridge
- Chatham University
- Visit Bloomfield
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.